


Diving

by Littlewinns



Category: Supergirl (TV 2015)
Genre: Gen
Language: English
Status: Completed
Published: 2019-01-11
Updated: 2019-01-11
Packaged: 2019-10-08 08:43:41
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,834
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17383367
Author URL: https://archiveofourown.org/users/Littlewinns/pseuds/Littlewinns
Summary: Winn goes to say goodbye to Ms. Grant before she heads off on her travels. Set during 2x02.





	Diving

**Author's Note:**

> I originally wrote this to be the start of something else; but it was way too big an outline, and I've already got a fic like that (which I *am* getting back to).
> 
> Anyway, this was already written, and I really like getting feedback. So enjoy.

Winn knocked, tentatively, on the open glass door of the office. It was late, and Miss Teschmacher wasn't at her desk. Maybe no-one was in? Even though he'd gone there of his own free will, he kind of hoped no-one was in. 

Not really wanting to be heard, he cried "Hello?" into the office; and was chagrined when he heard a response from out on the balcony.

"Out here, Winn."

Nervously, he stepped inside, and headed out toward the balcony doors; and stood there was Cat Grant, facing out into the night, sipping on what Winn guessed was very, very good scotch.

Silently, without any other acknowledgement of his presence, she moved out her free hand, and deposited something on the ledge next to her.

A second glass.

Winn took the invitation for what it was, and moved to join her.

"I just came to say goodbye, Ms. Grant," he said, stepping out onto the threshold, "I heard you were leaving us."

"I heard _you_ already had," she softly quipped back, "Strictly speaking, security shouldn't be letting you in the building."

"They like me," he said, shrugging.

"They're _supposed_ to like me," she replied, with a healthy dose of self-aware irony.

She handed him his glass, and said, "Tell me, Winslow: what is it that's so important that you felt you could waive your notice period? Your obligations to me and my company?"

Her words were harsh, but her tone was gentle; as though her tyrannical reputation was merely a private joke between the two of them.

This wasn't like her. Certainly, his relationship with Ms. Grant had improved a lot over the last year, in the sense that she'd learned his name; but he'd never been present during her softer moments that Kara had. This was new.

"It's classified, Ms. Grant," Winn replied, taking a sip of his drink as he did so. It was ASTOUNDINGLY good.

"Good," she said, firmly, "That means it's probably worth it."

"What about you? I mean, you're not _really_ leaving Catco behind, are you?" he asked.

"We have to dive, Winn. Embrace new challenges, do the unexpected thing. As you've already discovered for yourself," Ms. Grant answered, wistfully. "Your new job? Does it frighten you?"

He thought for a moment. "No," he said, before taking another moment and adding, "...and yes."

"Then it's definitely worth it," she commented, taking another sip of scotch.

"There's a lot riding on me now. Here, no-one notices what I do; unless I screw up. There..." he pondered, considering his new position at the DEO, "...It's the same. But _there_ a screw-up could mean life or death. It's... a lot to take in." 

Winn focused back on Ms. Grant. "What about you? What are you gonna do?"

"I... haven't decided yet. Spend more time with Carter... spend more time with Adam, even. Reassess my priorities. And then..."

"Try to take over the world?" Winn interrupted; which, to his surprise, made Ms. Grant blurt out a short laugh. "No need to be coy, Ms. Grant. World domination has always been considered a viable career path in the Schott family," he carried on, with a wry smile, "Anything I can do to help with that?"

"You already have a job," she replied.

"Yeah," he said, regaining his composure, "But I've always liked working for you, Ms. Grant. And, if it's a worthy cause, I'd be honoured to work for you again."

"Can I tell you a secret, Winn?" she said, turning to face him, leaning her hip into the balcony wall. "I've always liked you working for me, too."

And then, for the first time Winn could remember, Cat Grant smiled at him. and then, something even more unlikely happened.

She began to seem nervous.

"There is... _something_ you can do for me," she said, absently drawing her finger around the rim of her glass, before looking back up at him with hopeful eyes.

He'd never seen this side of her before: vulnerable, but with a hint of... was she _flirting_ with him?

"Uhhh," he stammered, "Is this about to get weird?"

He watched her raise a questioning eyebrow, and he panicked.

"I mean, don't get me wrong, Ms. Grant, I think you're a slow sip of whiskey, but my therapists have already said the words 'Oedipal Complex' more times than I'm really comfortable with, so if this is going to get weird-"

She raised an index finger to silence him, but didn't say a word. 

Instead, she searched his eyes, mouth slightly agape. Winn noticed the wind, lightly teasing her hair. The only way the scene could have been sexier was if she'd actually brought her finger up to his lips.

It had _SO_ gotten weird.

Winn's mind raced. First things first: Never. Tell. Anyone. Ever. Don't even hint at it. Get ready to move and change your name if you have to-

"...No, Winn," Cat said, finally lowering her hand, "That was... not what I had in mind."

"Oh," Winn said, relieved; before the full mortifying force of what he'd said hit him. 

" _Ohhhhh_."

Cat turned back to face the busy city sky, and sought comfort in her scotch.

"Oedipal Complex? You have an... unusual relationship with your mother?"

"Kind of," Winn said, with a thousand-yard stare, "I haven't seen her in nearly twenty years-"

"I... don't think I need the details on that," she said, trying to move on as quickly as possible; before adopting an encouraging tone, and adding, "The 'slow sip of whiskey' thing wasn't bad, though." 

"I think I stole it from somewhere," he said, with the knowledge of how much this would haunt him for years to come. "Ms. Grant... I am so, so, sorry-"

"No. Don't apologise," she interrupted, "It was a bold position to take; and you're going to need that."

"Um.... okay," he said, apprehensively, "What for?"

"Because I want you to find someone, Winn."

Winn floundered. He'd heard all the words, and he knew what they all meant, but...

"I don't understand," he said.

Cat drew herself up, the momentary discomfort from Winn's outburst now gone, and said, "That's what I want you to do, while I'm gone. I want you to find someone, someone that matters to you."

Winn almost spoke, but Cat interrupted, "No. Not someone that matters to you. Someone for whom _you_ matter."

"I... matter to people," Winn protested.

"No, you don't," Cat said. Winn was prepared to defend himself, but she spoke first, "Not the way they matter to you. And I know you know that. You knew it on Kara's first day here, and you knew it for two years after that; and I know you know it now, because you wouldn't be leaving her behind if you didn't."

She turned to face him again, leaning closer.

"It's time to _move on_. Not a dalliance, not another hopeless crush, and certainly not pretending you've moved on while secretly pining away. And it won't come to you on its own; so you have to decide what you want; and then go for it full speed.

"It's time to _dive_."

And then, she went back to her drink.

Winn was stunned. He knew Cat had known about his feelings for Kara... but he didn't know she _understood_ them so completely.

It didn't seem like a good time to mention that he wasn't leaving Kara behind at all.

"And what if what I want..." he said, remembering all the times in his life where he'd previously tried to fulfil Cat's wish and failed, "...doesn't want me back?"

"Doesn't matter. It _can't_ matter," she said, with a hint of frustration, "I have been married four times; and there wasn't a single one of them where I wasn't prepared to let my heart SHATTER when it all went wrong. Nothing else is worth it.

"But if you need incentive, perhaps consider that if you haven't put yourself into the kind of love story you deserve by the time I get back; I am going to be very, very upset with you."

There was a moment of silence as Winn contemplated her threat.

"Well, we wouldn't want that, would we?" he joked; although he put no effort into making it seem funny.

"No, you certainly do not," Cat said, "Now, drink up. I think I'd like to have some more time alone, and I can't do that with you hovering."

Ah. Back to her old self. Winn begrudgingly knocked back the rest of his drink, burning the back of his throat; before letting his eyes settle on the empty glass as he figured out what to do next.

There was one more thing he wanted to say. It didn't even seem like that big a deal. Hadn't it already been implied? But he couldn't seem to get the words out.

"Is there something else, Winn?"

"Yes, Ms. Grant..." Winn replied; realising, if he said it out loud... he'd be committed. Right now, he had a get-out clause. There was nothing anyone could hold him to. But saying the words would mean he was locked in. He'd have to follow through.

And the thought terrified him.

But she wanted him to bold. _Be bold, Winslow._

"I promise... that I'll try."

He didn't feel bold saying the words; and from Cat's change in body language, he got the feeling she wasn't impressed either.

It wasn't scorn. He was prepared for scorn. But he'd never seen her do _pity_ before. 

It didn't suit her. 

"Doesn't Master Yoda have very specific opinions about trying?" she asked, pointedly.

"Master Yoda only had an evil Empire to deal with. He wasn't trying to get women to like me," Winn replied, in what he hoped was good humour. "Also, he's a puppet."

"You were doing so much better when you were propositioning me," she said, matter-of-factly.

"I really am sorry about that."

"Stop apologising. Self-loathing has never gotten you anywhere," she said. He fought the urge to apologise for apologising.

"Sorry." _Dammit._

" _Stop it,_ " she said, returning to familar, comforting scorn; "And there are women that like you just fine, Winn. But if you don't like yourself enough to think you're worth their time, you never will be.

"So... go do something about that," she said, shooing him away as she watched the city.

Winn stepped out off the balcony and into the office, before he froze in place. There was one more thing...

"Catherine?"

She SPUN the moment she'd heard it, eyes wider than usual; but still, only mildly more shocked than she had been a few minutes before.

"Yes? _Winslow_?" she said. It had been much as Winn had expected: she encouraged the boldness, but had very particular feelings about it being used with her.

"I'm going to miss you," he said.

"I'll miss you, too, Winslow. Now hurry along."

He nodded, and headed back out of the office. He was out of earshot before she said the last thing she had to say.

"Go make me proud."

**Author's Note:**

> The slow sip of whiskey thing was, in fact, stolen; from Aaron Sorkin's Sports Night. I apologise for nothing.


End file.
